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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Annapolis Guesthouse - Completely Separate Space
2 bedrooms, 3 beds, 1 private bathroom
29 Aug – 3 Sept
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4.87 out of 5 average rating, 215 reviews
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds
24–29 Aug
New place to stay
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA and Beaches
3 bedrooms, 5 beds
12–17 Aug
4.91 out of 5 average rating, 22 reviews
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
2–7 Aug
New place to stay
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
14–19 Aug
4.97 out of 5 average rating, 96 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 366 reviews
Guest favourite
Home in Annapolis
Royal Hue House Style & Comfort
3 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds
16–21 Aug
4.97 out of 5 average rating, 139 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 359 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
16–21 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Newly Renovated Downtown Charm, Game Room, Patio
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds
16–21 Aug
4.97 out of 5 average rating, 100 reviews